US4868215AExpiredUtility

Substituted N-aroyl N'-phenyl urea compounds

72
Assignee: DOW CHEMICAL COPriority: Jul 26, 1982Filed: Sep 24, 1984Granted: Sep 19, 1989
Est. expiryJul 26, 2002(expired)· nominal 20-yr term from priority
Inventors:Barat Bisabri-ErshadiRaymond H. Rigterink
A01N 47/34C07C 275/54
72
PatentIndex Score
8
Cited by
19
References
23
Claims

Abstract

N-aroyl N'-phenyl ureas having the formula ##STR1## wherein: Ar is a substituted phenyl, pyridyl or pyrimidinyl radical wherein the substituents are chloro, bromo, fluoro C 1 -C 3 alkyl or C 1 -C 3 alkoxy, with the proviso that at least one substituent is positioned ortho to the carbonyl group; R 3 and R 4 are individually H or C 1 -C 4 alkyl or together they form the group ##STR2## Y is O or S; X 1 , X 2 , X 3 and X 4 are individually H, halogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, alkylcarbonyl, alkoxycarbonyl, C 1 -C 3 alkylthio, NO 2 , CN or NR 5 R 6 wherein R 5 and R 6 are H or C 1 -C 3 alkyl with the provisos that at least one of X 1 , X 2 , X 3 or X 4 is other than H and (a) when three of X 1 , X 2 , X 3 or X 4 are H, the fourth substitution cannot be halogen or alkyl, (b) when X 1 and X 3 are H, X 2 and X 4 cannot both be halogen, (c) when X 2 and X 3 are H, X 1 and X 4 cannot be both halogen, (d) when X 1 and X 4 are hydrogen, X 2 and X 3 cannot both be halogen and R is a C 1 -C 4 haloalkyl, haloalkoxy or haloalkylthio group which possess insecticidal properties.

Claims

exact text as granted — not AI-modified
We claim: 
     
       1. A compound having the formula ##STR12## wherein X 1 , X 2 , X 3  and X 4  are individually H, Cl or CH 3  with the proviso that at least two of X 1 , X 2 , X 3  and X 4  are other than H and at least one is CH 3  and R is haloalkoxy. 
     
     
       2. Compound of claim 1 wherein R is OCF 3 , OCF 2  CHCl 2 , OCF 2  CHF 2 , OCF 2  CHFCl, OCF 2  CHFBr, OCF 2  CHFI or OCFClCHFCl. 
     
     
       3. Compound of claim 2 wherein R is OCF 2  CHF 2 , OCF 2  CHFCl or OCF 2  CHFBr. 
     
     
       4. Compound of claim 3 wherein X 1  is H, X 2  and X 3  are both CH 3  and R is OCF 2  CHFCl. 
     
     
       5. Compound of claim 3 wherein X 1  is H, X 2  and X 3  are both CH 3  and R is OCF 2  CHF 2 . 
     
     
       6. Compound of claim 3 wherein X 1  is H, X 2  and X 3  are both CH 3  and R is OCF 2  CHFBr. 
     
     
       7. Compound of claim 3 wherein X 1  and X 3  are both CH 3 , X 2  is H and R is OCF 2  CHF 2 , OCF 2  CHFCl or OCF 2  CHFBr. 
     
     
       8. Compound of claim 3 wherein X 1 , X 2  and X 3  are CH 3  and R is OCF 2  CHF 2 , OCF 2  CHFCl or OCF 2  CHFBr. 
     
     
       9. Compound of claim 3 wherein X 1  is methyl and X 2  and X 3  are chloro. 
     
     
       10. A method of killing and/or controlling insects which comprises applying to the insects, the insect larvae or their habitats an insecticidally effective amount of a compound having the formula ##STR13## wherein X 1 , X 2 , X 3  and X 4  are individually H, Cl or CH 3  with the proviso that at least two of X 1 , X 2 , X 3  and X 4  are other than H and at least one is CH 3  and R is haloalkoxy. 
     
     
       11. Method of claim 10 wherein R is OCF 2  CHF 2 , OCF 2  CHFCl or OCF 2  CHFBr. 
     
     
       12. Method of claim 11 wherein X 1  and X 3  are both CH 3  and X 2  is H. 
     
     
       13. Method of claim 11 wherein X 2  and X 3  are both CH 3  and X 1  is H. 
     
     
       14. Method of claim 11 wherein X 1 , X 2  and X 3  are all CH 3 . 
     
     
       15. A composition comprising an insecticidally effective amount of at least one compound having the formula ##STR14## wherein X 1 , X 2 , X 3  and X 4  are individually H, Cl or CH 3  with the proviso that at least two of X 1 , X 2 , X 3  and X 4  are other than H and at least one is CH 3  and R is haloalkoxy. 
     
     
       16. Composition of claim 15 wherein R is OCF 3 , OCF 2  CHCl 2 , OCF 2  CHF 2 , OCF 2  CHFCl, OCF 2  CHFBr, OCF 2  CHFI or OCFClCHFCl. 
     
     
       17. Composition of claim 16 wherein R is OCF 2  CHF 2 , OCF 2  CHFCl or OCF 2  CHFBr. 
     
     
       18. Composition of claim 16 wherein X 1  is H, X 2  and X 3  are both CH 3  and R is OCF 2  CHFCl. 
     
     
       19. Composition of claim 16 wherein X 1  is H, X 2  and X 3  are both CH 3  and R is OCF 2  CHF 2 . 
     
     
       20. Composition of claim 16 wherein R 1  and R 2  are both F, X 1  is H, X 2  and X 3  are both CH 3  and R is OCF 2  CHFBr. 
     
     
       21. Composition of claim 16 wherein X 1  and X 3  are both CH 3 , X 2  is H and R is OCF 2  CHF 2 , OCF 2  CHFCl or OCF 2  CHFBr. 
     
     
       22. Composition of claim 16 wherein X 1 , X 2  and X 3  are CH 3  and R is OCF 2  CHF 2 , OCF 2  CHFCl or OCF 2  CHFBr. 
     
     
       23. Composition of claim 16 wherein X 1  is methyl and X 2  and X 3  are chloro.

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